You wouldn't spend shit at the shop on a good example. Get a PPI from a good mechanic.
These particular cars are some of the most robust and dependable cars ever made by GM. These were the basis for cop cars and taxis. The Fleetwoods and the Roadmasters with the towing package came with all the cop heavy duty stuff (heavy duty suspension, oil cooler, trans cooler, different rear end ratio, etc). But they are robust even without that stuff, and hell you can add an oil cooler and trans cooler if you really want to for cheap.
1994-1996 models had the LT-1 V8 and 4160e transmission. The LT-1 is a goddamn Corvette engine. In this application it is tuned more for torque than horsepower. 1992 Corvette LT-1s had an issue with valve stem seals. Not an issue with later Vettes or this application. With routine maintenance it is bulletproof. I shit you not. 4160e's that fail are usually not maintained, dogged, or tow too heavy of shit. The so-called common problems are due to that stuff. And the common problems are actually cheap and easy to fix if caught early, but you don't tow or dog your cars so fvck it. I highly recommend Amsoil trans fluid, that is good stuff.
The two main electrical gremlins are window rollers (fix them with teflon rollers, problem solved forever) and the power antenna(just get the damn thing fixed or leave it up and unplug at the connector). That is it. These things have good electronics.
I am not just talking shit to you. If the wife liked these, I would buy one. I absolutely love these cars, the end of an era and they are fvcking tanks. And since she currently insists on having a Mustang GT, we need one car that is FWD to navigate the snow. I am getting pretty active in the classic car scene, and know my stuff. If I had the cash I would start dealing in classic cars. And these Caddys are a classic, for sure.
My sincere advice to you, my friend: buy a house with a garage, or rent an apartment with one. Get one of these cars, because you know you love them. Garage it and make it your weekend and roadtrip car for the next 20 years. You can afford it, easy. This is a car that will not break your wallet. And get it soon, because examples in great shape are starting to appreciate. Hell, drive it on weekends for a couple years and sell it at no loss or a profit, the market is so up on these.